Gambling Time

Walk into the marbled main hall of the Casino de Monte Carlo and you find amidst the glitz and glamour, the smell of desperation. For every restrained tourist that sets a limit and sticks to it, there’s a dozen half-cut Mediterranean losers chasing their losses. It’s a race they’ll never win. Mortgages won’t be paid. The dream of the big win is just that. Rarely does it arrive but your money is taken with politeness personified and if you’re a resident of the Principality you are barred from gambling as a condition of living in what’s known as a sunny place for shady people. The Monagasque go and find other places to gamble big and yacht racing is a preferred sport.

©Mitch Pearson /

The 2021 Sydney-Hobart is serving up a thriller where only the brave dare to venture. It’s been a heck of a race so far. Tough and uncompromising, even some of the most experienced professionals are calling it the hardest race for a very long while. The retirements came thick and fast into that first night as boats and bodies broke under a sickness-inducing swell and an unrelenting breeze. The wise kept their powder dry, reefed down and slugged it out, keeping one eye on boat preservation and ignoring the leaderboard. You certainly couldn’t win the race in that first 24 hours but you could lose big time.

The glamour boats played the same game with the professionals onboard earning their money calling for conservatism and adopting a ‘hang in there’ mentality. The weather routers knew that this was a race of transitions with monster high pressure filtering up the racetrack that had the ability to turn the tables.

First it was the heavy upwind flyer ‘Law Connect’ that was setting the pace in the big breezes but Black Jack, the aptly named vessel of the benched Peter Harburg sailing under the Yacht Club de Monaco flag, hung in there safe in the knowledge that as the winds abated, their time would come. And sure enough it did, in spectacular fashion. Down the eastern seaboard coast of Hobart, it was a classic ocean racing duel as the two boats criss-crossed the rhumb line, keeping watch on the hard-driving Scallywag just behind but well in touch who has been playing catch-up all race and has its tail up.

©Rolex / Andrew Francolini

With just over 50 miles left to run as I write this, Black Jack is thundering down to the Tasman Island turning point at 11.6 knots, a couple of clicks faster than the chasers with around 10 miles in the bank and preparing for ocean racing’s biggest gambling stretch up the Derwent and into West Hobart.

It’s a place that has zero respect for form or standings and many a story is offered by those that really know this stretch of water of “woulda, coulda, shoulda.” Black Jack holds the cards for now and with its light airs pedigree is in pole position for a stunning victory if they can hold their nerve, ride their luck and eke out the final few hours. The navigator and wind spotters will be on red alert and every ounce of guile and local knowledge will be required to get home up the final 11 nautical miles and lift the John H Illingworth Challenge Cup – the ultimate line honours trophy in world sailing.

©Mitch Pearson /

This is a cruel race and with the 100 footers all packed tightly and the hard-driving 80 footer of Grant Wharington within shouting distance, lady luck that mean mistress could well play her part. If you’re not glued to the tracker on this one, there’s not a lot more we can do for you. The 2021 Sydney-Hobart is a cracker. It’s gambling time for the leaders and we have one heck of a race in store over the coming hours.

Stay tuned.

4 thoughts on “Gambling Time

  1. Thanks! I didn’t know that residents of Monaco are prohibited from gambling there. Merry Christmas to you and yours!

    Randy Needham (Rando) Cell 201-259-5831 (OK text/SMS)


    1. Hey, living in Monaco and not being tempted to waste any money in the casinos sounds pretty nice. More money to sail the Mediterranean!


  2. I love your prose. If I knew nothing about sailing, it would still be a great read. Thanks a lot. I wish that I could write like you!

    Liked by 1 person

  3. Brilliant piece of writing as usual and captures the essence of the race. I just spent 2 hours glued to the tracker as Celestial and (2x previous winner) Ichi Ban slugged it out up storm bay and the Derwent. Continuing the battle they’ve been running for 3 days. Celestial ends up corrected time leader (potentially the winner but we don’t know for a day or two… which in itself is awesome) by about 3 minutes, but what an incredible struggle. Brilliant to watch. Thanks again for your lovely article


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